Hydrochloric Acid → Methyl 2-[2-(chloromethyl)phenyl]acetate

HRID 850159Notes

Reaction equation

HRID 850159 reaction equation
[ClH:1].[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=[O:12])[O:3]1.[CH3:13]O>>[Cl:1][CH2:2][C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:5][C:4]([O:3][CH3:13])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 780921,4-dihydro-3H-2-benzopyran-3-one

Product 1

HCID 9855748Methyl 2-[2-(chloromethyl)phenyl]acetateYield 98%

Procedure

Gaseous hydrogen chloride was bubbled through a solution of 3-isochromanone (2.0 g, 13.5 mmol) in methanol (30 ml) for 0.5 hour at room temperature and the reaction stirred for a further 2 hours. The methanol was removed under reduced pressure and the residue was dissolved in dichloromethane and dried. Removal of the solvent gave methyl 2-chloromethylphenylacetate (2.62 g, 98%) as an oil which was used without further purification; 1H NMR (270 MHz)δ: 3.70(3H,s), 3.81(2H,s), 4.68(2H,s), 7.22-7.40(4H,m) ppm.

Workup

  1. customThe methanol was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customdried
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-3e294d149e754a96bb9e6298b4c24f3b
Source dataset
uspto-grants-2000_01
Patent number
US06015905

Reaction notes

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